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molecular formula C12H27OP B122868 Tributylphosphine oxide CAS No. 814-29-9

Tributylphosphine oxide

Cat. No. B122868
M. Wt: 218.32 g/mol
InChI Key: MNZAKDODWSQONA-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US04190729

Procedure details

A one gram quantity of Co(acetate)2. 4H2O and 9 grams triphenylphosphine oxide were charged to an autoclave with 100 cc methanol and 30 cc methylnaphthalene. The reactor was pressured to 3200 psi with an approximately equimolar mixture of hydrogen and carbon monoxide and heated to 180° C. with stirring. The reaction was allowed to proceed for 5 hours. The reactor was cooled and vented, and the reaction product was analyzed and shown to contain ethanol (21.3%), methyl acetate (9.8%), dimethylacetal (15.9%) and acetic acid (5.1%). The products were distilled and the cobalt remained in a soluble form in the distillation residue which consisted primarily of methylnaphthalene. The absence of a solid coating or precipitate on the distillation flask was noted. The distillation residue was returned to the reactor with additional methanol, and found to display high catalytic activity under carbonylation conditions as employed in this example. Thus it is demonstrated that the catalyst can be retained in soluble form by use of phosphine oxide stabilizer, and recycled in a form suitable for use upon application of carbonylation conditions. Similar results to the foregoing can be obtained if tributylphosphine oxide or other tertiary phosphine oxides are substituted for the triphenylphosphine oxide.
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
[Compound]
Name
Co(acetate)2
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
9 g
Type
reactant
Reaction Step Three
Quantity
30 mL
Type
reactant
Reaction Step Three
Quantity
100 mL
Type
solvent
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
[Compound]
Name
dimethylacetal
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Seven

Identifiers

REACTION_CXSMILES
[C:1]1([P:7](=[O:20])([C:14]2C=C[CH:17]=[CH:16][CH:15]=2)[C:8]2C=C[CH:11]=[CH:10][CH:9]=2)C=C[CH:4]=[CH:3][CH:2]=1.CC1C2C(=CC=CC=2)C=CC=1.[H][H].[C]=O.C(OC)(=O)C>C(O)(=O)C.C(O)C.CO>[CH2:1]([P:7](=[O:20])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH2:3][CH3:4] |^3:33|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)O
Step Two
Name
Co(acetate)2
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Three
Name
Quantity
9 g
Type
reactant
Smiles
C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O
Name
Quantity
30 mL
Type
reactant
Smiles
CC1=CC=CC2=CC=CC=C12
Name
Quantity
100 mL
Type
solvent
Smiles
CO
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[H][H]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[C]=O
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)(=O)OC
Step Six
Name
dimethylacetal
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Seven
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(=O)O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
180 °C
Stirring
Type
CUSTOM
Details
with stirring
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The reactor was cooled
DISTILLATION
Type
DISTILLATION
Details
The products were distilled
CUSTOM
Type
CUSTOM
Details
Similar results to the foregoing

Outcomes

Product
Details
Reaction Time
5 h
Name
Type
product
Smiles
C(CCC)P(CCCC)(CCCC)=O

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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